Lithium hydroxide, monohydrate → HCID 58946092, compound

HRID 747861Notes

Reaction equation

HRID 747861 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([C:11]([C:14]3[C:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:16][O:17][C:18]=3[CH3:19])=[N:12][CH:13]=2)[CH:10]=1)=[O:4].O.[OH-].[Li+]>O.CO>[CH3:19][C:18]1[O:17][N:16]=[C:15]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]=1[C:11]1[N:9]2[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[CH:7][C:8]2=[CH:13][N:12]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 24849792HCID 24849792, compound

Product 1

HCID 58946092HCID 58946092, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 3-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,5-a]pyridine-6-carboxylic acid methyl ester ( 0.25 g, 0.75 mmol) in water (6 mL) and methanol (3 mL) was added lithium hydroxide monohydrate (0.21 g, 5 mmol) in one portion. The reaction mixture was stirred for 4.5 h at room temperature. After evaporation (removal of methanol), the remaining mixture was extracted with diethyl ether. Then the aqueous layer was acidified to pH˜5 with aqueous HCl (2N). The light yellow precipitate was collected by filtration and washed with water to afford the title compound (0.2 g, 83%) as light yellow solid. MS: m/e: 320.1 [M+H]+.

Workup

  1. customAfter evaporation (removal of methanol)
  2. extractionthe remaining mixture was extracted with diethyl ether
  3. filtrationThe light yellow precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-5f95ebb399424642989c3351266f3267
Source dataset
uspto-grants-2008_07
Patent number
US07399769B2

Reaction notes

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